Season 10 is supposed to be set during the 2008-2009 school year based on when the series started (S1 2001-2002, S2 2002-2003, S3 2003-2004, S4 2004-2005, S5 2005-2006, S6 2006-2007-semester 1, S7 2006-2007-semester 2, S8 2007-2008-semester 1, S9 2007-2008-semester 2). This is shown also when any class graduates and is says the graduating year. This means that when Riley is looking at the most valuable player list the most current blank spot should have been 2008-2009, not 2010-2011, which is the current year.
When Drew is tied up naked in front of the school at the beginning of the episode, he asks the principal (Snake) to please get his "clothes". The camera pulls back just enough that you can see he's wearing jeans and is really only shirtless.
When Coach Armstrong discovers Drew wrapped to the pole he asks him who did this to him even though Drew has duct tape over his mouth and is unable to give an audible answer.